Hydroxybenzofluorenones and process of making same



Patented Aug. 17, 1937 UNITED ST ATENT OFFICE HYDROXYBENZOFLUOREN ONES AND PROCESS OF Grald Bonhote, Basel Society of Chemical Switzerland MAKING SAME Switzerland, assignor to Industry in Basle, Basel,

No Drawing. Application November 21, 1936, Serial No. 112,141. In Switzerland November 4 Claims.

in which X and Y represent two adjacent carbon atoms of an aromatic ring of the benzene series, are red powders dissolving in caustic alkalies, preferably in the presence of assistants, such as Turkey red oil, to red-violet solutions. They react with diazo compounds with formation of a20- dyestuffs. Their alkali salts are further characterized by an excellent affinity for the cellulose fiber. They are therefore suitable for producing fast tints according to the methods used in the production of ice colors. Thus, for example the l-hydroxy-3,4-benzofluorenone, combined on the vegetable fiberwith diazotized 4,4-dichloroaminodiphenylether, produces a Bordeaux tint; with diazotized 4-amino-3-methoxyazo-benzene or 4- amino-3-methoXy-6-methyl- 4- chloroazobenzene extraordinarily fast black tints are obtained.

The following examples illustrate the invention, the parts being by weight:

Example 1 25 parts of 2-hydroxynaphthalene-3-phenylketone are stirred for 2 hours at 120-130 C. with 75 parts of aluminium chloride and then for 1 hour at EEO-150 C. The viscous melt becomes solid on cooling. It is pulverized and gradually introduced into dilute hydrochloric acid While stirring, whereupon stirring is continued for some time. The condensation product is filtered, dissolved in hot dilute caustic soda solution, and filtered from any impurities which may be present. The clear solution is acidified with hydrochloric acid of per cent. strength, whereby the D new condensation product precipitates. When recrystallized from alcohol its melts at 163 C. The new product corresponds to the formula Example 2 10 25 parts of 2 hydroxynaphthalene 3 -(4 methyl) -phenyl-ketone are stirred for 2 hours at 120-130 C. with 75 parts of aluminium chloride and then for 1 hour at 140-150" C. The viscous melt becomes solid on cooling. It is pulverized and gradually introduced into dilute hydrochloric acid while stirring, whereupon stirring is continued for some time. The condensation product is filtered, dissolved in hot dilute caustic soda solution, and filtered from any impurities which may be present. The clear solution is acidified with hydrochloric acid of 10 per cent. strength, whereby the new condensation product precipitates. When recrystallized from alcohol its melts at 178 C. The new product corresponds to the formula What I claim is:-

1. Process for the manufacture of hydroxybenzofiuorenones, consisting in treating with acid condensing agents ortho-hydroxy-diarylketones obtainable from halides of the 2,3-hydr0xynaphthalene carboxylic acids and aromatic bezene hydrocarbons.

2. The hydroxybenzofiuorenones of the formula in which X and Y represent two adjacent carbon 5 3. The hydroxybenzofluorenone of the formula.

V C 10 V atoms of an aromatic ring of the bezene hydrocarbon series, which products are red powders dissolving in dilute caustic alkalies on addition of assistants to red-violet solutions 4. The hydroxybenzofiuorenone of the formula.

CH5 V 7 GERALD B NHOTE. 

